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Preheat oven to 425 degrees. Cut stems from beets. Rinse and pat dry. Place the beets into a square of foil. Drizzle with olive oil, fold up ends of foil around beets and roast in the oven for about 1 hour. Beets are done when the tip of a knife can be inserted easily. Remove from oven and allow to cool. When cool enough to handle, rub the skin off the beets with your fingers. It should slip off easily; then slice into cubes.
Cut bottom and top off squash and remove skin, if desired. Cut into 1/2-inch slices; then cube. Place on a sheet pan. Drizzle with oil and bake in the oven for 20-25 minutes, or until tender. Remove from oven and let cool.
In a small bowl, whisk together olive oil, parsley, shallot, lemon zest and juice until well combined. Season with sea salt and pepper, to taste.
In a large bowl, toss roasted beets, arugula and sliced pears with parsley dressing and serve.